cis-3(S)-(6-amino-9H-purin-9-yl)-1(R)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopentane | 210163-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: cis-3(S)-(6-amino-9H-purin-9-yl)-1(R)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopentane
• 英文别名: tert-butyl N-[(1R,3S)-3-(6-aminopurin-9-yl)cyclopentyl]-N-hydroxycarbamate
• CAS: 210163-20-5
• 化学式: C₁₅H₂₂N₆O₃
• 分子量: 334.378
• InChiKey: YREGLQMLOYKNSK-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  cis-3(S)-(6-amino-9H-purin-9-yl)-1(R)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopentane 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到N-[(1R,3S)-3-(6-Amino-purin-9-yl)-cyclopentyl]-hydroxylamine; hydrochloride
  参考文献：
  名称：

  Syntheses of novel hydroxylamine carbanucleosides

  摘要：

  Enantiomerically pure 4'-hydroxylamino-adenine-derived carbanucleosides have been synthesized as isosteric 4'-hydroxymethyl analogs to carbovir, ddA, and aristeromycin. The key steps in the syntheses involved an enzymatic desymmetrization, two subsequent Mitsunobu reactions, and a highly diastereoselective ruthenium tetroxide-mediated dihydroxylation, overcoming the syn-directing effect seen in osmium tetroxide-mediated dihydroxylations. Hydroxylamino-propane analogs were also synthesized through similar methodology to afford adenine and cyclopropylamino purine analogs to acyclovir. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00359-7
• 作为产物：
  描述：

  (1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ol 在 palladium dihydroxide 、 palladium on activated charcoal 偶氮二甲酸二苄酯 、 氨 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 100.0h， 生成 cis-3(S)-(6-amino-9H-purin-9-yl)-1(R)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopentane
  参考文献：
  名称：

  Syntheses of novel hydroxylamine carbanucleosides

  摘要：

  Enantiomerically pure 4'-hydroxylamino-adenine-derived carbanucleosides have been synthesized as isosteric 4'-hydroxymethyl analogs to carbovir, ddA, and aristeromycin. The key steps in the syntheses involved an enzymatic desymmetrization, two subsequent Mitsunobu reactions, and a highly diastereoselective ruthenium tetroxide-mediated dihydroxylation, overcoming the syn-directing effect seen in osmium tetroxide-mediated dihydroxylations. Hydroxylamino-propane analogs were also synthesized through similar methodology to afford adenine and cyclopropylamino purine analogs to acyclovir. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00359-7

文献信息

• Syntheses of novel hydroxylamine carbanucleosides
  作者：Mark J. Mulvihill、Marvin J. Miller

  DOI：10.1016/s0040-4020(98)00359-7

  日期：1998.6

  Enantiomerically pure 4'-hydroxylamino-adenine-derived carbanucleosides have been synthesized as isosteric 4'-hydroxymethyl analogs to carbovir, ddA, and aristeromycin. The key steps in the syntheses involved an enzymatic desymmetrization, two subsequent Mitsunobu reactions, and a highly diastereoselective ruthenium tetroxide-mediated dihydroxylation, overcoming the syn-directing effect seen in osmium tetroxide-mediated dihydroxylations. Hydroxylamino-propane analogs were also synthesized through similar methodology to afford adenine and cyclopropylamino purine analogs to acyclovir. (C) 1998 Elsevier Science Ltd. All rights reserved.